Manchester City and Manchester United have both been knocked out of the Champions League at the group stage, marking the first time more than one Premier League club has failed to advance from the round robin.
Since the competition increased to include more than just the league winners from each domestic league, England has never had two clubs exit at the group stage.
Manchester City was always up against it heading into Matchday 6 as it required a victory over Bayern Munich while also hoping for Napoli to fail to win against Villarreal. Despite winning 2-0 at the Etihad Stadium, Roberto Mancini's side finish third in Group A as Napoli also recorded a 2-0 victory in Spain.
Manchester United was in control of its own destiny as it headed to Switzerland to face Basel, knowing that a draw would be enough to send it into the last 16. However, goals from Marco Streller and Alexander Frei put Basel through at United's expense, despite a late counter from Phil Jones.
It is only the third time in 17 Champions League campaigns that United has not advanced from the group stage. The previous occasions were in 1994-95 and 2005-06.